Just when you thought Sterling Brown‘s night couldn’t get any worse … we’ve now learned the NBA player was on a 1st date with a woman when he was tased in a Walgreens parking lot.

TMZ Sports obtained the file and video from the internal investigation into the Jan. 26 incident — which made national news for the way Milwaukee PD officers aggressively handled the Bucks player, whose only mistake was parking in a handicap space.

Cops took Brown down to the ground andtased him — despite the fact video evidence showed he never resisted or seemed to pose a threat.

Now, we’ve learned the woman who was with Brown that night told cops she barely knew Sterling because they were on their first date.

When cops put the woman into a police cruiser to take her home after Brown was arrested — cops apologized to her for ending the date … and joked with her about the evening.

In fact, one of the cops joked about Brown sliding into her DMs.

The unidentified woman laughed at the jokes — and cops ultimately told her to “give him another chance.”

Brown was never charged with a crime — but he later filed a lawsuit against the PD claiming he was violently mistreated.